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Bailey Island flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was CA $1,641, price is now CA $1,518 per person
CA $1,518
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Maine Mall and Casco Bay Lines Ferry Terminal are located nearby.
River View Resort

River View Resort

2.5 out of 5
Price was CA $3,599, price is now CA $3,449 per person
CA $3,449
per person
Oct 9 - Oct 13
found 24 hours ago
Roundtrip flight included
Ottawa (YOW) to Portland (PWM)
Stay at this motel in Bethel. Enjoy free WiFi, free parking, and 4 outdoor pickleball courts. Our guests praise the helpful staff in our reviews. Popular attractions Sunday River and Bethel Pathway are located nearby.
Mayville Union House

Mayville Union House

3 out of 5
Price was CA $3,975, price is now CA $3,833 per person
CA $3,833
per person
Oct 9 - Oct 13
found 24 hours ago
Roundtrip flight included
Ottawa (YOW) to Portland (PWM)
Book a stay at this business-friendly B&B in Bethel. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Sunday River and Bethel Pathway are located nearby.
The Elizabeth Inn and Restaurant

The Elizabeth Inn and Restaurant

3 out of 5
Price was CA $3,501, price is now CA $3,421 per person
CA $3,421
per person
Oct 9 - Oct 13
found 24 hours ago
Roundtrip flight included
Ottawa (YOW) to Portland (PWM)
Stay at this B&B in Bethel. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Sunday River and Bethel Hill Common are located nearby.
The Bethel Resort & Suites

The Bethel Resort & Suites

3 out of 5
Price was CA $3,442, price is now CA $3,373 per person
CA $3,373
per person
Oct 9 - Oct 13
found 24 hours ago
Roundtrip flight included
Ottawa (YOW) to Portland (PWM)
Book a stay at this ski resort in Bethel. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Sunday River and Bethel Historical Society are located nearby.

Top Bailey Island hotels deals

Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Free cancellation
The price is CA $129 per night
CA $129
CA $141 total
Sep 13 - Sep 14
includes taxes & fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's Point are located nearby.
Pool
Breakfast included
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free cancellation
The price is CA $182 per night
CA $182
CA $202 total
Sep 1 - Sep 2
includes taxes & fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and State Theatre are located nearby.
Pool
Hot tub
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Free cancellation
The price is CA $134 per night
CA $134
CA $146 total
Aug 20 - Aug 21
includes taxes & fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby.
Breakfast included
Pet-friendly
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Free cancellation
Reserve now, pay when you stay
The price is CA $425 per night
CA $425
CA $470 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maine Mall and Casco Bay Lines Ferry Terminal are located nearby.
Hot tub
Spa
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Free cancellation
Reserve now, pay when you stay
The price is CA $145 per night
CA $145
CA $160 total
Sep 8 - Sep 9
includes taxes & fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby.
Pool
Hot tub
Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

2.5 out of 5
90 Maine Mall Rd South Portland ME
Free cancellation
The price is CA $165 per night
CA $165
CA $180 total
Sep 2 - Sep 3
includes taxes & fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby.
Breakfast included
Free airport shuttle
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Bailey Island attractions

Bailey Island Bridge

9.2/10 (10 reviews)
Find out about the history of Bailey Island when you spend time at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.
See properties

Frequently asked questions

How much are vacation packages to Bailey Island?
Vacation packages, which provide both flights and hotels in Bailey Island, start at just CA $1,518. Make your travel fantasies come to life and secure your vacation with Travelocity today.
Where can I get the best vacation package deals for Bailey Island?
With around 400 partner airlines and 1,000,000 properties across the globe, you can't beat Travelocity. Browse our comprehensive range and score an incredible Bailey Island package deal. Don't you love it when travel is that easy?
Why should I book my Bailey Island vacation bundle with Travelocity?
With exceptional service, customer support available 24/7 and some of the most perfect escapes on offer, you'll never wander alone. And if you find a better price, we'll match it. That's our Price Match Guarantee.
Can I save money on my Bailey Island car rental if I bundle it with my hotel or flight?
Bundling your bookings into a Bailey Island vacation package will leave you with a nice chunk of spare change. You can bundle a car and flight; a hotel, flight and car; or a hotel and car. You won't find a better way to explore the greater Bailey Island region than with your own ride. You can also add experiences and tours to your Travelocity package.

Photos of local treasures

Browse Bailey Island vacation photos for more inspiration

A rocky shoreline with a boat, a house, and a forest in the background.
A wooden pier extending into calm waters with a red and white boat docked at the end.
A green netted buoy attached to a wooden post by a curved metal hook, with a wooden fence and a body of water in the background.
A sign for Morse Lobster, open Monday to Sunday, with a lobster and lobster traps displayed.
A wooden bridge over water with a yellow kayak, boats, and a motel in the background.